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By Matt Rocheleau, Town Correspondent

A South Boston man arrested over the weekend and accused of soliciting sex online from someone he believed was a 15-year-old girl had worked in Boston's public school system for 36 years as a teacher and administrator before retiring two years ago, school officials confirmed today.

John Caputo, 63, pleaded not guilty to charges of soliciting sex for a fee and enticing minors in Dorchester District Court today.

Undercover officers recently posed as a 15-year-old girl in online exchanges with Caputo and two other men, Boston police said yesterday. Acting separately, each of the three men then “knowingly agreed’’ to meet with the person they believed was an underage girl “with the intent of engaging in various sexual activities,’’ police said.

When the three men arrived separately at the arranged meeting locations, various points along Gallivan Boulevard in Dorchester, they were arrested by officers Friday afternoon and evening, prosecutors said. Beforehand, police had obtained the identities of the men who had made online contact with the officers posing as a 15-year-old.

Caputo has been charged with soliciting sex for a fee twice before, in 1998 and again in 2000, according to Suffolk District Attorney Office spokesman Jake Wark. Both of Caputo's prior cases were continued without a finding, Wark said. No further details were available on either of the old cases, the spokesman added.

Caputo was a Boston Public Schools teacher and administrator from Sept. 1973 to Aug. 2009, most recently employed at Madison Park High School in Roxbury, school officials confirmed today.

When asked about the nature of Caputo's retirement two years ago, city schools spokesman Matt Wilder said via e-mail today: "We wouldn't have any indication as to why John Caputo decided to retire when he did."

And, when asked whether Caputo had ever been accused of misconduct or disciplined during his tenure, and whether the school department knew about his two prior charges of soliciting sex for a fee, the spokesman said: "We wouldn't be able to share information that may or may not be included in this former employee's personnel file."

Prosecutors asked today that Caputo be held on $10,000 cash bail and that he be ordered to stay away from anyone under age 17 while his case is pending, according to Wark. A judge ordered that Caputo be held on $7,500 cash bail and that he stay away from anyone under age 17 while his case is ongoing.

Prosecutors asked that the other two men arrested Saturday, Daniel Klim, 38, of Cambridge, and John Nguyen, 24, of Randolph, each be held on $7,500 cash bail and be ordered to stay away from minors while their cases are still in court, Wark said. Both of those requests were granted in each case by Judge Shannon Frison in Dorchester District Court today.

After their arrests, all three men had posted an initial $300 bail and appeared in court Monday. Caputo is represented by attorney John Henneberry and will return to court on Dec. 7, officials said. Klim is represented by attorney Frank Camera and will return to court on Dec. 27. Nguyen is represented by attorney Pam Murphy and will return to court on Dec. 2.

“As repugnant as it is to most of us, the commercial sexual exploitation of children is very real,” Suffolk District Attorney Daniel F. Conley said in a statement. “It exists because of the demand illustrated here. Boston Police, Suffolk prosecutors, and law enforcement across New England are focusing on this issue like never before, and those who want to buy sex with children can count on more investigations like this one.”

“The Boston Police Human Trafficking Unit is committed to ending exploitation of young women and will continue to be proactive in doing this by continuously seeking various ways to address this issue,’’ a police statement said.